Style

woman wearing boots

BOOTS, Paris Texas. Photograph courtesy Acielle / STYLE DU MONDE.

The Definitive 2019 Fall Boot Guide

Working on the annual breakdown of boot trends is not unlike watching the Emmys. Every year we know to expect a few repeat appearances, one definite breakout star (clearly, Phoebe Waller-Bridge), and always, always a couple of newcomers that surprise and delight. What we’ve learned from doing our due diligence thus far? Knee-highs are back, Chelseas never left, cowgirls can be chic, kittens are always ready to party, and the chunkier the heel, the sexier the shoe. And now for the nominees…

CHUNKY COMBAT

Heavy-duty street-stompers may not be for everyone, but when teamed with good tailoring, these sleek spin-offs morph into the most modern styling hack ever.

  1. Clergerie boots Clergerie boots
    Clergerie
    boots
    goop, $695
    SHOP NOW
  2. Chloe boots Chloe boots
    Chloé
    boots
    goop, $1,340
    SHOP NOW
  3. hiraeth boots hiraeth boots
    Hiraeth
    boots
    goop, $650
    SHOP NOW
  4. valentino boots valentino boots
    Valentino
    boots
    MatchesFashion, $995
    SHOP NOW

Wear them with

  1. g. label shelly pleated-back top g. label shelly pleated-back top
    G. Label
    shelly pleated-back top
    goop, $375
    SHOP NOW
  2. proenza schouler high waisted paper bag pants proenza schouler high waisted paper bag pants
    Proenza Shouler
    pants
    goop, $1,090
    SHOP NOW
  3. Totême coat Totême coat
    Totême
    coat
    goop, $1,100
    SHOP NOW

    WESTERN REBOOT

    Citified, with a slick country twang, these pointy-toed classics are the perfect counterpoint to every pair of cropped bottoms you own.

  1. girl sitting on chair girl sitting on chair girl sitting on chair
    Acne Studios
    boots
    goop, $800
    SHOP NOW

CHELSEA 2.0

Faux snakeskin, high shine, lug soles—we didn’t think it was possible, but this historically no-BS boot has stepped up its game and gotten…cooler. Do yourself a favor and get the cashmere socks.

  1. agl navy patent leather boots agl navy patent leather boots
    AGL
    boots
    goop, $395
    SHOP NOW
  2. atp atelier olivia snake boots atp atelier olivia snake boots
    ATP Atelier
    boots
    goop, $695
    SHOP NOW
  3. Dries Van Noten boots Dries Van Noten boots
    Dries Van Noten
    boots
    Net-a-Porter, $840
    SHOP NOW
  4. BOTTEGA VENETA BOOTS BOTTEGA VENETA BOOTS
    Bottega Veneta
    boots
    Bottega Veneta, $990
    SHOP NOW

Wear them with

  1. apiece apart jacket apiece apart jacket
    Apiece Apart
    jacket
    goop, $625
    SHOP NOW
  2. the elder statesman socks the elder statesman socks
    The Elder
    Statesman
    socks
    MatchesFashion,
    $155
    SHOP NOW
  3. the elder statesman socks the elder statesman socks
    The Elder
    Statesman
    socks
    MatchesFashion,
    $300
    SHOP NOW
  4. Nanuska parka Nanuska parka
    Nanushka
    parka
    goop, $620
    SHOP NOW

    HIGH AND MIGHTY

    The taller, the chicer, if you ask us. These statement-making knee-highs may be great with a swingy hemline, but we’re breaking all the rules by wearing ours with jeans tucked in.

  1. woman standing with stella mccartney boots woman standing with stella mccartney boots woman standing with stella mccartney boots
    Stella McCartney
    boots
    goop, $1,035
    SHOP NOW

BLOCK PARTY

Hardly new kids on the, ahem, block, these stacked beauties deliver durability, walkability, versatility—all the -ilities—a shoe we can count on in every season.

  1. by far sofia black leather boots by far sofia black leather boots
    BY FAR Shoes
    boots
    goop, $510
    SHOP NOW
  2. ATP Atelier boots ATP Atelier varenna boots
    ATP Atelier
    boots
    goop, $570
    SHOP NOW
  3. Tabitha Simmons Lela boots Tabitha Simmons Lela boots
    Tabitha Simmons
    boots
    goop, $795
    SHOP NOW
  4. Victoria Beckham square boots Victoria Beckham square boots
    Victoria Beckham
    boots
    goop, $1,365
    SHOP NOW

Wear them with

  1. wolford mat opaque tights wolford mat opaque tights
    Wolford
    Tights
    goop, $61
    SHOP NOW
  2. wolford black socks wolford black socks
    Wolford
    Socks
    goop, $29
    SHOP NOW
  3. wolford sheer tights wolford sheer tights
    Wolford
    Tights
    goop, $49
    SHOP NOW
  4. wolford sheer socks wolford sheer socks
    Wolford
    Socks
    goop, $17
    SHOP NOW

    THE KITTEN

    They have the allure of after-dark heels and the sensibility of sturdy boots, along with the works-with-everything-in-your-wardrobe factor. You can’t lose.

  1. AGL booties AGL booties AGL booties
    AGL
    booties
    goop, $515
    SHOP NOW